Stefanos Tsitsipas leads 5 to 1 over 6 singles meetings since 2021. Last meeting on 04/11/2023 at Rolex Paris Masters - Paris.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 04/11/2023 | Rolex Paris Masters - Paris | Semi-final | indoor hard | Dimitrov | 6-3 6-7(1) 7-6(3) |
| 29/12/2022 | United Cup - Australia | Round robin | hard | Tsitsipas | 4-6 6-2 7-6(4) |
| 11/05/2022 | Internazionali BNL d'Italia - Rome | Round 2 | clay | Tsitsipas | 3-6 7-5 6-7(4) |
| 05/05/2022 | Mutua Madrid Open - Madrid | Round 3 | clay | Tsitsipas | 3-6 3-5 |
| 22/04/2022 | Barcelona Open Banc Sabadell - Barcelona | Round 3 | clay | Tsitsipas | 6-1 6-4 |
| 25/10/2021 | Erste Bank Open - Vienna | Round 1 | indoor hard | Tsitsipas | 7-6(6) 6-4 |
| indoor hard | Dimitrov 1 - 1 Tsitsipas |
| hard | Dimitrov 0 - 1 Tsitsipas |
| clay | Dimitrov 0 - 3 Tsitsipas |
| 2023 | Dimitrov 1 - 0 Tsitsipas |
| 2022 | Dimitrov 0 - 4 Tsitsipas |
| 2021 | Dimitrov 0 - 1 Tsitsipas |
161 wins, 103 losses since 2021 (61.0%).
Last matches: D V V V D
256 wins, 122 losses since 2021 (67.7%).
Last matches: V V V D V
Stefanos Tsitsipas leads 5 to 1 over 6 singles meetings since 2021.
On 04/11/2023, at Rolex Paris Masters - Paris (Semi-final): Grigor Dimitrov won 6-3 6-7(1) 7-6(3).